Out of curiosity Brandon, any reason you want to go with two dogs for specific purposes rather than one versatile?
Personally, I can definately see the advantages of that path. Just got finished grouse and woodcock hunting with some good friends with field trial proven setters. A lot of fun to watch and nice and small dogs in the house. I think the number of birds we shot over the setters and the versatiles (in this case Pudelpointers) was about the same, but they wouldn't come close to being able to retrieve waterfowl in the water compared to a versatile. Not a knock against them at all, just not what they're bred for (kind of like labs and pointing :-)).
That said I think it could be really cool to have a setter or brittany and lab or chessie for duck hunting. Could be problematic if you only have one of each and it gets hurt during hunting season, but could be a lot of fun.
Anycase, what is your thought in this approach?